I worked on several early web systems, mostly shopping, POS, GIS and related in various industries. I did create a few systems in C, using many custom tools an

I worked on several early web systems, mostly shopping, POS, GIS and related in various industries. I did create a few systems in C, using many custom tools and the only way I can describe the final results is that they were rather restrictive. Even with a template system, plugin abilities and other modern features you are essentially locked into your initial design goals. Code iteration is limited by the change/compile/deploy cycle - with the compile cycle being rather time heavy. Secondly, the fragility of debugging crash bugs requires a full-blown debugger environment or developing a nice stack-dump system ,which I eventually wrote. In other words, the biggest problem was lack of tools, a lack of support for quick dev cycles, and support for such a system. If I had to do it over again today, I'd use an embedded compiler running in a fastcgi like daemon. This would allow you to speed up the dev cycle and be able to contain segfaults, memory leaks, and the like. QEMU or TCC would be a good start. Perhaps even a stripped down docker environment. Pure C in a fast-paced dev cycle is just too rigid and error-prone.